Two Work-Related Questions You Really Should Be Asking Yourself

Awhile back — maybe two years ago? — I was venting to my wife Megan. Though time has erased the precise details, my best guess would be that work was burning me down.

At the time I had a hand in running three businesses: a marketing consultancy now called Wunderbar LLC, a portfolio of iOS and Android apps, and a music tech startup called Closeup.fm. (Check out a killer Closeup case study on Hypebot here.) Factor in a wife, a child, a mortgage, a business partner, and various and sundry bills, and you begin to understand why I might feel weight on my shoulders.

Megan usually has wisdom to share, and she asked a question that stopped me in my tracks:

“If you knew your current circumstances weren’t going to change for awhile, what would you start doing differently right now?”

We often postpone certain beneficial choices, or a relaxing vacation, or the practice of contentment and joy, or the laying hold of sanity, while we wait for a more opportune time.

Don’t plan the romantic getaway just yet. The kids aren’t old enough.
 Don’t call it a day just yet. You may be exhausted, but you still have several items on your to-do list.
 Don’t go on a walk or take a nap or linger over lunch with a friend. Nope. Daylight is burning.

You need to double down, recommit. You must squeeze every lost drop of productivity out of yourself. You must delay gratification until… until… you’re so burned out you only have eyes to see what is broken, incomplete, or unsatisfying.

It’s ironic really: We choose unsustainable habits as the path to some ideal future. We kill ourselves to improve our circumstances. We turn a blind eye to alternatives, or we’re too tired to investigate.

Here’s a second question worth asking:

Are you even open to a more humane, more sustainable, and more effective way of pursuing true prospering?

For me, the answer to that second question, the kernel of wisdom, is more simple than I thought: Spend a portion of your waking hours enjoying life.

My conversation with me went something like this:

Why are you working so hard?

“So that my life will be better in the future.”

What does “better” look like?

[He rattles of a list of things like traveling, writing, studying another language, playing guitar, spending time with friends and family, and philanthropy.]

But couldn’t you work less and do all of those things now? [He falls into a thoughtful silence.]

So what about you?

Let’s assume for a moment that your ideal future will never show up on your doorstep.

If you knew with complete clarity that you were never going to…

• become independently wealthy
• have a baby
• get married
• get a promotion
• magically lose weight without changing your diet or exercising

…what incremental change would you make today?

I have started writing more (because I love it), running more (because it makes me less grumpy), and saving more (because I’m just as tired of trying to get rich quickly as I am of being broke).

What about you?

If you knew your current circumstances weren’t going to change for awhile, what would you start doing differently right now?

I’m learning that ideal futures are more like porch swings than mountaintops.